Abstract:  I will describe extremal surfaces in de Sitter space anchored at the future boundary I+. Since such surfaces do not return, they require extra data or boundary conditions in the past (interior). In entirely Lorentzian de Sitter spacetime, this leads to future-past timelike surfaces stretching between I±. Apart from an overall −i factor (relative to spacelike surfaces in AdS) their areas are real and positive. With a no-boundary type boundary condition, the top half of these timelike surfaces joins with a spacelike part on the hemisphere giving a complex-valued area. Motivated by these, we describe two aspects of “time-entanglement” in simple toy models in quantum mechanics. One is based on a future-past thermofield double type state entangling timelike separated states, which leads to entirely positive structures. Another is based on the time evolution operator and reduced transition amplitudes, which leads to complex-valued entropy. There are close parallels with pseudo-entropy which we will clarify.